Steven Kimes believes the poor really will inherit the earth. That’s why he quit his job, took his family to the streets, and became Portland’s most radical servant of the homeless.

THETRUTH IS, when you see a homeless person holding a sign at an intersection, you hit the gas and send silent agonized prayers skyward, hoping the stoplight doesn’t catch you. Because if you have to stop, you’ll have to admit that there is another human being right outside the window, begging for help. And when you don’t roll down the window to offer a hand, you’ll be forced to feel guilty.

This, clearly, is a lot of work to do to avoid parting with a dollar or a handful of nickels.

Kimes’s solution is more direct: he rolls down his window and offers socks. “Clean socks are gold out on the streets,” he says, hailing a homeless man in camo and handing him white tube socks and an energy bar. Cruising up near the Rose Garden, with “Black Celebration” (Depeche Mode’s national anthem of goth) moping from the stereo, Kimes doles out Gold Toes and granola. It’s nearly more than a brain programmed to demarcate humanitarian and hip into non-intersecting columns can handle. Kimes relishes the dichotomy.

“This is our life,” he screams over Dave Gahan’s heroin whine. “We’re not plugged into the crumbling empire.”

‘Every politican, every judge, every member of the church—they need to spend time on the street.’—Steve Kimes

He’s right, of course. And this, too, is a gift. Kimes is so driven by his desire to create this free-form utopia where the homeless gain self-sufficiency and the respect of the middle class while still keeping their eyes focused on the Lord that all shades of zealotry or general assholery in these types of comments are scoured away—even when he says things like “People with a high income have to give it away to get into heaven,” or preaches the perils of homosexuality in his sermons. His cause is just, his intentions righteous. Sometimes it’s better just to bite your tongue.

The man in the passenger seat, Mike DeSerio, knows all about the crumbling empire. He unplugged himself six months ago. He’d gone through a divorce. He hated his job. And he lived in Tampa, the glistening tit-tassel of Florida. Looking for inspiration, he sought direction from Google. He typed in the words “wilderness” and “Portland” and somehow found his way to one of Kimes’s many blogs. A Christian by trade, DeSerio was turned on by Kimes’s pro-service doctrine. He bought a one-way ticket and settled in on Kimes’s porch, where he slept for nearly three months until the weather got too cold.

Then he upgraded to the couch.

“I just felt the urge to be homeless, like God was telling me to do it,” DeSerio says, his imposing shaved head undercut by dorky black glasses. “So I came up and have sort of shadowed Steve to learn about the service he provides.”

In the ultimate sign of respect, Kimes—who runs in a world of grizzled men with handles like Ankles, Diver, Styxx, Slim, and Troll—gave DeSerio his very own nickname: Hammer. “We called him M.C. at first because he came from a middle class family,” Kimes explains, “but my wife said, ‘No, we should just call him Hammer. As in M.C. Hammer.’ We didn’t tell him why we named him Hammer for three months.”

With Hammer’s youthful muscle, Kimes’s three-pronged outreach has hummed of late. There’s the drive-by socking that goes into effect whenever Kimes is behind the wheel; there’s his home, which he opens to a rotating cast of homeless people, whose numbers would likely raise the ire of housing authorities; and then there are the four meals that Anawim serves weekly for upward of four hundred people.

Fridays are the most intense. Kimes and Hammer cover more than fifty miles in their rickety van, hitting up most every food pantry and Dumpster between Gresham and St. Johns in order to fill Anawim’s coffers.